How to plan a trip to Maui in 7 easy steps

Planning a trip to Maui? How exciting! But also… how overwhelming! All you want to be doing is counting down the days to the start of your vacation in Maui. Yet, the list of things to consider is long enough to make your head spin. Even more so when this is your first trip to Maui.

No stress! I’m here to help you plan your trip to Maui so you can look forward to the vacation of your dreams.

Maui isn’t the kind of destination that allows for much spontaneity: Parks require reservations, rental car inventory is limited, and the best tours and restaurants are booked out way in advance.

My 7-step Maui vacation planning guide will lead you through. Learn when to visit Maui, how to find the perfect place to stay, and which tours to book. Insider tips for visiting Maui are sprinkled throughout.

Sounds like a plan? Then here’s the best way to plan a trip to Maui like a pro!

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1. Set your dates

Maui is packed with palm-fringed beaches, scenic coastal trails, dreamy resorts, intriguing sights, and exciting adventures. With so many amazing things to do, defining that Maui itinerary is no easy task.

Will you spend most of your time on the beach and add an activity here and there to mix things up? Or is your Maui trip a once-in-a-lifetime experience and do you plan on crisscrossing the island to experience it to the fullest? It makes all the difference in the number of days you need on the island.

How many days do you need in Maui?

How many days can you set aside? Spending 5 days in Maui is an absolute minimum but I’d recommend 8 days for the ultimate relaxation. That corresponds to the average length of stay on the Hawaiian Islands as analyzed by the Hawaii Tourism Authority.

Of course, if have the luxury of time (and money), then you might as well make it a 10-day Maui itinerary. You’ll never run out of things to do on the Valley Isle anyway.

Ideally, you keep the first day (or two) free to recover from jet lag or simply unwind and plan your favorite Maui things to do on the following days.

Be sure to leave a day or two free at the end of your Maui trip. After all, tours get rescheduled occasionally. That might be due to the weather, due to landslides (which can occur on the Road to Hana in East Maui), rough ocean waters, or shy whales. It’s always safe to have a backup day or two to fall back on.

And if everything plays out as planned, you can use these extra days to relax or to follow up on Maui travel tips from the concierge or from people you met along the way.

Don’t overload your itinerary, as in don’t go planning a Haleakala sunrise tour and a sunset dinner cruise on the same day. You want to be able to enjoy your vacation, not race around and end up exhausted by the time you return home. Remember this when determining how many days in Maui you set aside for exploring.

When is the best time to visit Maui?

As for any trip, it’s best to avoid school holidays and general holiday seasons. Easier said than done when planning a family trip to Maui, I know. But for honeymoons, babymoons, and other couples retreats, I’d recommend the off-season: May, September, October, and the first half of November. There’s a reason why the weeks after the summer break are referred to as couples season on Maui.

Another element to factor in is the weather. Maui only has two seasons: winter and summer season. Rain occurs at any time throughout the year and showers don’t tend to last more than a few minutes to a few hours. But overall, the chance of showers is higher in winter.

Occasionally, in winter, a stretch of rainy days can occur. You’re more likely to experience rainfall in West Maui during the winter months. The higher north the rainier, so I’d avoid Kapalua then. South Maui has a drier climate and is the better choice for a winter vacation.

The situation is a bit different during the summer months when the waters in South Maui tend to be choppier than the waters in West Maui.

When is the cheapest time to visit Maui?

Overall, the weather doesn’t impact the prices all too much since snowbirds still prefer the relatively warm Maui winter over their colder winter at home. So, it’s not surprising that the most expensive months to visit Maui entirely coincide with the popular holiday periods.

Here’s a breakdown of the tourist seasons in Maui:

Traveling during the off-season results in better deals on accommodations and car rentals. It allows for impromptu visits and the overall vibe on the island is more relaxed.

What’s it like to visit Maui during the high season?

Oftentimes, you can’t change the circumstances and there’s little to no wiggle room when it comes to travel dates. When traveling during the peak season, the planning part is even more crucial. But if you’re prepared to book ahead even more than usual, then you’ll be fine.

It’s also a matter of managing your expectations. I’ve vacationed in Maui during the peak season and my trip was as amazing as it was during the off-season.

Yes, there was a line at the rental car desk. But, I eventually did get the car I had booked. No, I didn’t get to dine at Mama’s Fish House as a walk-in. Instead, I enjoyed a delicious dinner elsewhere. Yes, the sunset dinner cruise was at full capacity. But, it didn’t affect the overall experience all too much.

Understand that seasonality might slightly impact your Maui vacation but it certainly won’t spoil it. Not if you make your reservations well in advance, anyway.

2. Book your flights to Maui

Now that your dates are set, it’s time to secure your bookings starting with your flights. Here are some things to consider when booking your flights to Hawaii.

Which airlines offer direct flights from the mainland?

Maui is home to three airports: Kahului Airport, Kapalua Airport, and Hana Airport.

Kahului Airport (airport code: OGG) is the airport you’ll most likely be flying into. Direct flights from the mainland are available with the following airlines: Air Canada, Alaska Airlines, American Airlines, Delta, Hawaiian Airlines, United Airlines, Southwest Airlines, and WestJet.

Kapalua airport is served by local airlines for inter-island flights since it only accepts propeller planes. Hana Airport is the tiniest of the three and only accepts single-engine propeller planes.

When is the best time to book tickets to Maui?

The best flight deals tend to be available when you book your tickets between 4 and 2 months before departure. But of course, it all depends on the season.

That’s where Google Flight alerts come in. I usually have my alerts in place 6 months before I travel to Maui. Here’s how it works: Set your departure city, your destination city, and your dates. Then, toggle on the “track prices” button on the results page. Then, head over to Expedia to book the flight.

Trends indicate that January and February are the cheapest months to fly to Maui. Surprisingly so, because that coincides with high season and higher accommodation prices.

3. Book your Maui accommodation

This step is the focus of this website and it’s the most important decision you’ll make when planning your trip to Maui. Where you stay in Maui can make or break your Maui vacation.

That’s why you’ll find our curated lists of the best places to stay in Maui organized by area, accommodation type, and travel type. Click the menu item of your choice for our hand-picked suggestions.

Here’s an intuitive overview that’ll help you in your decision process.

What’s the best area to stay in Maui?

The most popular Maui resort areas are West Maui and South Maui.

West Maui features the resort towns of Kaanapali and Kapalua with the quieter coastline of Napili in between.

South Maui features Kihei, the luxurious Wailea resort community, and a more laid-back Makena.

If you’re looking to spend a night or two in Hana, then you’ll likely be staying at the Hana-Maui Resort.

Other parts of Maui to stay in are Paia and Haiku on the North Shore and Kula in Upcountry Maui near Haleakala National Park. These areas are far less touristy. Pleasant vacation rentals and cozy guesthouses make up the accommodation offer in these Maui areas.

Discover our Maui area guide which includes a map of Maui and more info on the various Maui towns.

Maui hotel vs Maui vacation rental?

Hotels in Maui come with amazing pools, water parks, entertainment, a selection of restaurants, and a certain level of service. The size of the hotel rooms and the lack of privacy are possible disadvantages.

Vacation rentals come with more space, a kitchen, and more privacy. Then again, you have to compromise on daily maid service and a range of facilities such as restaurants and pools. Unless your condo is part of a resort complex, then you get the best of both worlds.

Eventually, it depends on your expectations from the trip to Maui. Are you looking for a romantic getaway away from the crowds? Or for a family-friendly hideaway that offers plenty of space? Maybe you’re looking for the best pool for your teens? Or simply an affordable place to stay that’s centrally located?

So, it’s mostly a matter of preference but also a matter of budget. Condo rentals tend to be more affordable, hotels are more expensive and beach villa rentals are the priciest. Then again, each option comes with its hidden costs such as resort fees for hotels, taxes for vacation rentals, and parking costs for both.

Discover more information on this topic in our Maui accommodation guide or browse my selection of Maui hotels and resorts and Maui vacation rentals. Rest assured that every one of my suggestions is hand-picked and very well-researched. I only include places that this discerning traveler herself would consider booking.

Should you book a Maui vacation package?

First things first: All-inclusive Maui vacation packages aren’t an option simply because there aren’t any all-inclusive hotels on Maui. At least not the leave-your-wallet-at-home kind of all-inclusive hotels. Most Maui trip packages include airfare, accommodation, a rental car, and maybe even an activity.

Sometimes you might save when you book deal packages to Maui on Expedia. Unfortunately, though, that’s not always the case. So, it’s still important to do the math before you book your trip to Maui.

When should you book your Maui accommodation?

Again here, the early bird catches the worm. Make your first booking, with free cancelation, about 6 months before departure and even longer if you plan on traveling to Maui in peak season. At that point, you’ll have ample choice in accommodation, room types, and dates.

Lock in the price and then regularly check whether prices have dropped. If they have, simply modify your booking or make a new booking before canceling the original one to avoid the risk of ending up empty-handed.

I have to admit that I sometimes book two or three accommodations, especially when I don’t have my entire itinerary figured out yet. Once I know what my Maui trip will look like, I keep the booking of my choice and cancel the other ones.

4. Book your Maui rental car

Do you need a rental car in Maui? Most likely yes, you do. If you plan on venturing beyond the swaying palms of your Maui vacation accommodation, then a rental car is a must.

What type of rental car do you need?

Rental cars on Maui come in all shapes and sizes but especially the Jeep Wrangler and the Ford Mustang are in high demand. The best car for you is the one that gives you the Maui experience you’re dreaming of. A compact car will do just as well as a fancy model.

There’s only one small unpaved section on the back road from Hana that’s restricted for all rental vehicles, 4-wheel drives included. If you take the risk and get in trouble on that particular off-road section, then the car rental company will charge you for roadside assistance or towing.

So, a Jeep certainly isn’t a requirement but, if you feel that it complements the island experience, especially on your first Maui vacation, then by all means go ahead.

Where can you find the best car rental deals?

I recommend Discount Hawaii Car Rental to score that perfect deal. It offers carefree booking (no credit card required), free cancelation, and excellent customer service. It’s my go-to car rental company when vacationing in Maui or any of the other Hawaiian islands.

When should you book your Maui rental car?

Islands can be a bit tricky when it comes to car rental. After all, relocation is not an option which results in limited inventory. That’s why it’s essential to book your rental car well ahead of time. I do it right after I booked my accommodations.

It gives you the luxury of locking in a price and regularly checking to see whether the price has dropped. If that’s the case, you can modify your booking or make a new booking and then cancel the original one.

5. Book your activities

Now that you have your flights, accommodations, and car booked it’s time to dive a little deeper. At this point, it’s important to have your Maui itinerary figured out, especially when you’re visiting in high season.

Which Maui attractions require reservations?

Even if you won’t be joining any tour and plan on visiting the island’s top attractions individually, there are some reservations to be made. This might not be mentioned in all Maui travel guides yet, as some of these sites have only recently implemented this reservation system.

Which Maui tours book out quickly?

In case you’ll be joining an excursion, then I’d certainly recommend booking these well in advance too, especially during the peak season. Popular activities in Maui are:

6. Book your restaurants

The next step in planning your trip to Maui may come as a surprise but even some restaurants require reservations. And for the most popular places to dine, the ever-alluring Mama’s Fish House for one, you’ll even need to book months ahead. A last-minute call from the hotel concierge won’t get you in.

It’s not that every single dinner needs to be planned for – especially during low season there is room for some spontaneity – but the special nights out do require an early reservation.

To be on the safe side, I usually book ahead for several evenings, especially when I’m vacationing in Maui during the peak winter season.

7. Practical arrangements when planning a trip to Maui

Now that you made it this far, you can sit back and start counting the days until you get to experience Maui. And with a Maui itinerary as balanced and well-planned as yours, you can look forward to a carefree trip.

Here are some finishing touches that might come in handy during your trip.

Alerts to sign up for

The wildfires that plagued Maui in 2023 were a dramatic reminder of the importance of alerts. With countless microclimates, the weather can often change within less than a mile. Here are two alerts worth signing up for when planning a trip to Maui:

Reports to sign up for

In addition to the safety alerts, some other interesting reports are worth signing up for. Especially so if you plan on spending lots of time in the ocean snorkeling or surfing.

Useful groups and websites to join

And finally, here are some websites that might be useful for arranging for beach and kids’ gear.

What to pack for Maui?

Maui’s warm climate makes it easy to minimize clothing. There’s no need to overpack. Here are some essentials to add to your Maui packing list.

Reef-safe sunscreen can be bought at a local shop. The same goes for beach gear.

Planning a trip to Maui FAQ

That’s it for this Mau trip planner. By now, your Maui vacation planning should be ready to go. All that’s left for you to do is count down the days until you can finally get on that plane and reap the fruits of your thought-out planning. Happy travels!